This study speculated on the details and meaning of making 『 Gunsan-leewoo-dochub』. This literary work recorded friendship in Gogunsando(Sunyoodo, Gunsan now) as a shelter during the Imjinwaeran of 1593. It expressed friendship with poetry, calligraphy and drawing between two scholars who were in different ages. They were Jo Young, an artist of the middle Joseon period and Kim Joo, a scholar. It consisted of a total of 18 pages centering on <Gunsan-leewoo-do>, a drawing by Jo Young: Jo Young's Jehwasi(Sino-Korean Poetry about Painting), Kim Joo's preface, Kwon Pil's Jehwasi and Jeungbyolsi, Park Gyeong-Rip's epilogue, and 2 pieces of poetry by Seongro. It contains both Jehwasi and drawing and is full of artistic and literary beauty of poetry, calligraphy and drawing. This is the first study on the 『Gunsan-leewoo-dochub』. Its making process and period were drawn from the making details. Also, this study found the friendship was true through works by literary people as friends. Therefore, the literary meaning of the 『 Gunsan-leewoo-dochub』 was analysed in three aspects: First, the 『Gunsan-leewoo-dochub』 was a leading literary work containing poetry, calligraphy and drawing. It has great meaning in that it expressed true friendship between Kim Joo and Jo Young beyond ages and kindred with art.
Second, it had meaning in that it recorded friendship during the war. They opened their hearts each other and depended on each other in fearful and pressing situation of war, through which they overcame the hard period. Third, it was jointly made by intellectuals of that time. After Jo Young died, they exchanged literary works while maintaining relationships. Thus, through the 『 Gunsan-leewoo-dochub』, we can understand that active communication and true friendship among intellectuals of that period existed beyond friendship only between Kim Joo and Jo Young. The 『Gunsan-leewoo-dochub』 is a work containing poetry, calligraphy and drawing and shows that there were true communication and friendship among people who exchanged although it recorded friendship between the two persons.